WO2021118159A1 - Heterocyclic compound, and organic light-emitting element comprising same - Google Patents

Abstract

The present specification relates to: a heterocyclic compound represented by chemical formula 1; and an organic light-emitting element comprising same.

Description

Heterocyclic compound and organic light emitting device comprising same

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0167113 filed with the Korean Intellectual Property Office on December 13, 2019, the entire contents of which are incorporated herein by reference.

The present specification relates to a heterocyclic compound and an organic light emitting device including the same.

The organic electroluminescent device is a type of self-luminous display device, and has a wide viewing angle, excellent contrast, and fast response speed.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.

The material of the organic thin film may have a light emitting function if necessary. For example, as the organic thin film material, a compound capable of forming the light emitting layer by itself may be used, or a compound capable of serving as a host or dopant of the host-dopant light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing the roles of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like may be used.

In order to improve the performance, lifespan or efficiency of the organic light emitting device, the development of a material for the organic thin film is continuously required.

A compound having a chemical structure that can satisfy conditions required for materials usable in an organic light emitting device, such as an appropriate energy level, electrochemical stability and thermal stability, and can play various roles required in an organic light emitting device according to a substituent Research on organic light emitting devices including

<Prior art literature>

U.S. Patent No. 4,356,429

The present application relates to a heterocyclic compound and an organic light emitting device including the same.

In an exemplary embodiment of the present application, a heterocyclic compound represented by the following Chemical Formula 1 is provided.

[Formula 1]

In Formula 1,

N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N,

R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and -NRR' or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or to form an aromatic heterocyclic ring,

L, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,

Ar is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; or -SiRR'R";

Wherein R, R' and R" are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 is a heteroaryl group of

a, d and e are the same as or different from each other and are each an integer from 0 to 4,

b is an integer from 0 to 3,

c is an integer from 0 to 2,

When a to e are 2 or more, the substituents in parentheses are the same as or different from each other.

In addition, according to an exemplary embodiment of the present application, the first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one organic material layer includes the heterocyclic compound represented by Chemical Formula 1 above. provides

The compound described herein may be used as an organic material layer material of an organic light emitting device. The compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in the organic light emitting device. In particular, the compound can be used as a material for a light emitting layer of an organic light emitting device. For example, the compound may be used alone as a light emitting material, two compounds may be used together as a light emitting material, and may be used as a host material of the light emitting layer.

In particular, the heterocyclic compound according to the present application has specific substituents at positions 1 and 3 of one benzene ring of dibenzofuran, and has a carbazole-based substituent on the other benzene ring, so an organic light emitting device including the same In this case, it has excellent characteristics of lifespan and efficiency.

1 to 3 are views schematically showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present application, respectively.

<Explanation of code>

100: substrate

200: positive electrode

300: organic layer

301: hole injection layer

302: hole transport layer

303: light emitting layer

304: hole blocking layer

305: electron transport layer

306: electron injection layer

400: cathode

Hereinafter, the present application will be described in detail.

In the present specification, "when a substituent is not indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( ² H, Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

In the exemplary embodiment of the present application, "when a substituent is not indicated in the chemical formula or compound structure" may mean that all positions that can come as a substituent are hydrogen or deuterium. That is, in the case of deuterium, deuterium is an isotope of hydrogen, and some hydrogen atoms may be isotope deuterium, and the content of deuterium may be 0% to 100%.

In an exemplary embodiment of the present application, in the case of "when no substituents are indicated in the chemical formula or compound structure," the content of deuterium is 0%, the content of hydrogen is 100%, etc. If deuterium is not explicitly excluded, hydrogen and deuterium may be mixed and used in the compound. That is, when expressing "substituent X is hydrogen", deuterium is not excluded, such as 100% hydrogen content and 0% deuterium content, and may mean a state in which hydrogen and deuterium are mixed.

In an exemplary embodiment of the present application, deuterium is an element having a deuteron consisting of one proton and one neutron as one of the isotopes of hydrogen as an atomic nucleus, hydrogen- It can be expressed as 2, and the element symbol can also be written as D or 2H.

In the exemplary embodiment of the present application, isotopes have the same number of protons (protons), but isotopes that have the same atomic number (Z), but different mass numbers (A) have the same number of protons Elements with different numbers of (neutrons) can be interpreted.

In an exemplary embodiment of the present application, the meaning of the content of specific substituents T% is T2 when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents is defined as T2. It can be defined as /T1×100 = T%.

That is, in one example,

20% of the content of deuterium in the phenyl group represented by means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and among them, if the number of deuterium is 1 (T2 in the formula), it will be expressed as 20% can That is, the 20% content of deuterium in the phenyl group may be represented by the following structural formula.

In addition, in the exemplary embodiment of the present application, in the case of "a phenyl group having a deuterium content of 0%", it may mean a phenyl group that does not contain a deuterium atom, that is, has 5 hydrogen atoms.

In the present specification, the halogen may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, more specifically, 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.

In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20. Specific examples include a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but are not limited thereto.

In the present specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like; The present invention is not limited thereto.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic refers to a group in which a cycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may be a different type of ring group, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like. The carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, more specifically 5 to 20. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2 ,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the heterocycloalkyl group includes O, S, Se, N or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic refers to a group in which a heterocycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may be a different type of ring group, for example, a cycloalkyl group, an aryl group, a heteroaryl group, or the like. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

In the present specification, the aryl group includes a monocyclic or polycyclic having 6 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic means a group in which an aryl group is directly connected or condensed with another ring group. Here, the other ring group may be an aryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or the like. The carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrethyl group a nyl group, a tetracenyl group, a pentacenyl group, an indenyl group, an acenaphthylenyl group, a 2,3-dihydro-1H-indenyl group, a condensed cyclic group thereof, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

When the fluorenyl group is substituted, it may have the following structural formula, but is not limited thereto.

In the present specification, the heteroaryl group includes S, O, Se, N or Si as a hetero atom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic refers to a group in which a heteroaryl group is directly connected or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms. Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolilyl group, naphthyridyl group, acridinyl group, phenanthrid Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group , dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilol group, spirobi (dibenzosilol), dihydrophenazinyl group, Phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10, 11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, Benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl group , pyrido [1,2-b] indazolyl group, pyrido [1,2-a] imidazo [1,2-e] indolinyl group, 5,11-dihydroindeno [1,2-b ] a carbazolyl group, and the like, but is not limited thereto.

In the present specification, the amine group is a monoalkylamine group; monoarylamine group; monoheteroarylamine group; -NH ₂ ; dialkylamine group; diarylamine group; diheteroarylamine group; an alkylarylamine group; an alkyl heteroarylamine group; And it may be selected from the group consisting of an aryl heteroarylamine group, the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene There is a nylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but is not limited thereto.

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied. In addition, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.

In the present specification, the phosphine oxide group is represented by _{-P(=O)R 101} R _{102 ,} R ₁₀₁ and R ₁₀₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. The phosphine oxide group specifically includes, but is not limited to, a diphenylphosphine oxide group, a dinaphthylphosphine oxide, and the like.

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, and is represented by _{-SiR 104} R ₁₀₅ R _{106 , R 104} to R ₁₀₆ are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. It is not limited.

As used herein, "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

The structures exemplified by the above-described cycloalkyl group, cycloheteroalkyl group, aryl group and heteroaryl group may be applied, except that the aliphatic or aromatic hydrocarbon ring or heterocycle that adjacent groups may form is not a monovalent group.

In the present specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent is substitutable, When two or more substituents are substituted, two or more substituents may be the same as or different from each other.

In the present specification, "substituted or unsubstituted" means C1 to C60 linear or branched alkyl; C2 to C60 linear or branched alkenyl; C2 to C60 linear or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine selected from the group consisting of It means that it is substituted or unsubstituted with one or more substituents, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above-exemplified substituents are connected,

Wherein R, R' and R" are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 is a heteroaryl group of

In an exemplary embodiment of the present application, a heterocyclic compound represented by Formula 1 is provided.

In particular, in Formula 1, the substituent of the carbazoles substituted on one benzene ring of dibenzofuran is a substituent having hole transport characteristics, and is substituted on the 1st position of the other benzene ring of dibenzofuran. N-Het is a substituent having an electron transport characteristic (Electron transport character moiety), it is characterized by a trisubstituted compound having an additional Ar substituent at the 3-position. That is, when Ar is not substituted, the 3rd position of dibenzofuran is relatively lacking in electrons, and as the 3rd position of dibenzofuran forms a substituent of Ar as shown in Formula 1 of the present application, electrons are abundant As a result, the stability of the structure is increased, and consequently, the lifespan and current flow of the organic light emitting device including the same are improved.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of Chemical Formulas 2 to 5 below.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,

Definitions of R1 to R10, N-Het, Ar, L, L1, L2, a, b, c, d, and e are the same as those in Formula 1 above.

In particular, in Formulas 2 and 3, when the carbazole-based substituent substituted for dibenzofuran is substituted at the 3rd or 4th position, the T _d (95%) value tends to be higher by about 10 to 40°C than in other cases. As a result, it has a characteristic particularly excellent in thermal stability. That is, in the case of Formulas 2 and 3, the carbazole-based substituent is substituted at the 3rd or 4th position, and as two substituents are formed at the 1st and 3rd positions of the opposite benzene ring, the molecular weight increases and the stability of the structure itself is improved. have increasing characteristics.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by Chemical Formula 6 or Chemical Formula 7 below.

[Formula 6]

[Formula 7]

In Formulas 6 and 7,

The definitions of R1 to R10, N-Het, L, L1, L2, a, b, c, d, and e are the same as the definitions in Formula 1 above,

Ar1 is a substituted or unsubstituted C6 to C60 aryl group,

X is O or S;

R11 to R15 are the same as or different from each other and each independently represent hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and -NRR' or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or to form an aromatic heterocyclic ring,

f is an integer of 0 to 3, and when f is 2 or more, the substituents in parentheses are the same as or different from each other.

In an exemplary embodiment of the present application, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.

In another exemplary embodiment, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C40 arylene group; Or it may be a substituted or unsubstituted C2 to C40 heteroarylene group.

In another exemplary embodiment, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or it may be a substituted or unsubstituted C6 to C40 monocyclic or polycyclic arylene group.

In another exemplary embodiment, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or it may be a substituted or unsubstituted C6 to C20 monocyclic arylene group.

In another exemplary embodiment, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or it may be a C6 to C20 monocyclic arylene group.

In another exemplary embodiment, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a phenylene group.

In an exemplary embodiment of the present application, R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and -NRR' or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic Or it may form an aromatic heterocyclic ring.

In another exemplary embodiment, R1 to R10 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and -NRR' or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic Or it may form an aromatic heterocyclic ring.

In another exemplary embodiment, R1 to R10 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C6 to C40 aryl group; and a substituted or unsubstituted C2 to C40 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 group An aromatic heterocycle may be formed.

In another exemplary embodiment, R1 to R10 are the same as or different from each other, and each independently hydrogen; C6 to C40 aryl group; and a C2 to C40 heteroaryl group substituted or unsubstituted with a C6 to C40 aryl group, or two or more adjacent groups are bonded to each other and substituted or unsubstituted with a C1 to C10 alkyl group or a C6 to C40 aryl group A C6 to C40 aromatic hydrocarbon ring or a C2 to C40 aromatic heterocycle unsubstituted or substituted with a C6 to C40 aryl group may be formed.

In another exemplary embodiment, R1 to R10 are the same as or different from each other, and each independently hydrogen; C6 to C20 aryl group; and a C2 to C20 heteroaryl group substituted or unsubstituted with a C6 to C20 aryl group, or two or more groups adjacent to each other are bonded to each other and substituted or unsubstituted with a C1 to C10 alkyl group or a C6 to C20 aryl group A C6 to C20 aromatic hydrocarbon ring or a C6 to C20 aryl group may be substituted or unsubstituted to form a C2 to C20 aromatic heterocyclic ring.

In another exemplary embodiment, R1 to R10 are the same as or different from each other, and each independently hydrogen; phenyl group; a carbazole group unsubstituted or substituted with a phenyl group; dibenzofuran group; and a dibenzothiophene group, or two or more groups adjacent to each other are bonded to each other to form a benzene ring; benzothiophene ring; benzofuran ring; an indole ring unsubstituted or substituted with a phenyl group; Alternatively, an indene ring unsubstituted or substituted with a methyl group or a phenyl group may be formed.

In an exemplary embodiment of the present application, R9 and R10 may be hydrogen.

In an exemplary embodiment of the present application, Ar is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; or -SiRR'R".

In another exemplary embodiment, Ar is a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, Ar is a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, Ar is a C6 to C40 monocyclic or polycyclic aryl group; Alternatively, it may be a C2 to C40 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C6 to C40 aryl group and a C2 to C40 heteroaryl group.

In another exemplary embodiment, Ar is a phenyl group; biphenyl group; naphthalenyl group; a dibenzothiophene group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group and a dibenzofuran group; Or it may be a dibenzofuran group.

In an exemplary embodiment of the present application, N-Het may be a substituted or unsubstituted monocyclic or polycyclic heterocyclic group including one or more N.

In another exemplary embodiment, N-Het may be a monocyclic or polycyclic C2 to C60 heterocyclic group that is substituted or unsubstituted, and contains 1 or more and 3 or less N.

In another exemplary embodiment, N-Het may be a monocyclic or polycyclic C2 to C40 heterocyclic group that is substituted or unsubstituted, and includes 1 or more and 3 or less N.

In another exemplary embodiment, N-Het may be a monocyclic or polycyclic C2 to C40 heterocyclic group that is unsubstituted or substituted with a C6 to C40 aryl group and contains 1 or more and 3 or less N.

In another exemplary embodiment, N-Het is a triazine group unsubstituted or substituted with a substituent; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted 1,10-phenanthroline group; a substituted or unsubstituted 1,7-phenanthroline group; a substituted or unsubstituted quinazoline group; Or it may be a substituted or unsubstituted benzimidazole group.

In another exemplary embodiment, N-Het is a triazine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group; a pyrimidine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group and a naphthyl group; a pyridine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group and a naphthyl group; a quinoline group unsubstituted or substituted with a phenyl group; 1,10-phenanthroline group unsubstituted or substituted with a phenyl group; 1,7-phenanthroline group unsubstituted or substituted with a phenyl group; a quinazoline group unsubstituted or substituted with a phenyl group or a biphenyl group; Or it may be a benzimidazole group unsubstituted or substituted with a phenyl group or a biphenyl group.

In an exemplary embodiment of the present application, the 1,10-phenanthroline group may be represented by the following Chemical Formula 1-1, and the 1,7-phenanthroline group may be represented by the following Chemical Formula 1-2.

[Formula 1-1]

[Formula 1-2]

In an exemplary embodiment of the present application, R, R' and R" are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or It may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, R, R' and R" may be the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group.

In another exemplary embodiment, R, R′ and R″ may be the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group.

In another exemplary embodiment, R, R′ and R″ may be the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 monocyclic aryl group.

In another exemplary embodiment, R, R' and R" may be the same as or different from each other, and each independently a C6 to C20 monocyclic aryl group.

In another exemplary embodiment, R, R' and R" may be a phenyl group.

In an exemplary embodiment of the present application, Ar1 may be a substituted or unsubstituted C6 to C60 aryl group.

In another exemplary embodiment, Ar1 may be a substituted or unsubstituted C6 to C40 monocyclic or polycyclic aryl group.

In another exemplary embodiment, Ar1 may be a C6 to C40 monocyclic or polycyclic aryl group.

In another exemplary embodiment, Ar1 may be a C6 to C40 monocyclic aryl group.

In another exemplary embodiment, Ar1 may be a C6 to C40 polycyclic aryl group.

In another exemplary embodiment, Ar1 is a phenyl group; biphenyl group; or a naphthyl group.

In an exemplary embodiment of the present application, R11 to R15 are the same as or different from each other and each independently, hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and -NRR', or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted C2 to C60 aliphatic Or it may form an aromatic heterocyclic ring.

In another exemplary embodiment, R11 to R15 are the same as or different from each other and each independently, hydrogen; a substituted or unsubstituted C6 to C60 aryl group; And it may be selected from the group consisting of a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, R11 to R15 are the same as or different from each other and each independently, hydrogen; a substituted or unsubstituted C6 to C40 aryl group; And it may be selected from the group consisting of a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, R11 to R15 are the same as or different from each other and each independently, hydrogen; C6 to C40 aryl group; And it may be selected from the group consisting of a C2 to C40 heteroaryl group.

In another exemplary embodiment, R11 to R15 are the same as or different from each other and each independently, hydrogen; C6 to C20 aryl group; And it may be selected from the group consisting of a C2 to C20 heteroaryl group.

In another exemplary embodiment, R11 to R15 are the same as or different from each other and each independently, hydrogen; phenyl group; dibenzofuran group; Or it may be a dibenzothiophene group.

In another exemplary embodiment, R15 may be hydrogen.

According to an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

In addition, by introducing various substituents into the structure of Formula 1, compounds having intrinsic properties of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, an electron transport layer material, and a charge generation layer material used in manufacturing an organic light emitting device into the core structure, the conditions required for each organic material layer are satisfied. substances can be synthesized.

In addition, by introducing various substituents into the structure of Formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic materials and diversifying the use of the material.

In addition, in an exemplary embodiment of the present application, the first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises a heterocyclic compound according to Formula 1 above; to provide.

In another embodiment, the first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes one heterocyclic compound according to Chemical Formula 1 provides

Specific details of the heterocyclic compound represented by Formula 1 are the same as described above.

In the exemplary embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

In another exemplary embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

In the exemplary embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the blue organic light emitting device. For example, the heterocyclic compound according to Formula 1 may be included in the host material of the blue light emitting layer of the blue organic light emitting device.

In the exemplary embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the green organic light emitting device. For example, the heterocyclic compound according to Formula 1 may be included in the host material of the green light emitting layer of the green organic light emitting device.

In the exemplary embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the red organic light emitting device. For example, the heterocyclic compound according to Formula 1 may be included in the host material of the red emission layer of the red organic light emitting device.

The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described heterocyclic compound.

The heterocyclic compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.

In the organic light emitting device of the present invention, the organic material layer may include an emission layer, and the emission layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer may include an emission layer, the emission layer may include a host material, and the host material may include the heterocyclic compound.

As another example, the organic material layer including the heterocyclic compound includes the heterocyclic compound represented by Chemical Formula 1 as a host, and may be used together with an iridium-based dopant.

In the organic light emitting device of the present invention, the organic material layer may include an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.

The organic light emitting device of the present invention includes a light emitting layer, a hole injection layer, and a hole transport layer. It may further include one or more layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

1 to 3 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to an exemplary embodiment of the present application. However, it is not intended that the scope of the present application be limited by these drawings, and the structure of an organic light emitting device known in the art may also be applied to the present application.

Referring to FIG. 1 , an organic light emitting device in which an anode 200 , an organic material layer 300 , and a cathode 400 are sequentially stacked on a substrate 100 is illustrated. However, it is not limited to such a structure, and as shown in FIG. 2 , an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.

3 illustrates a case in which the organic material layer is multi-layered. The organic light emitting diode according to FIG. 3 includes a hole injection layer 301 , a hole transport layer 302 , a light emitting layer 303 , a hole blocking layer 304 , an electron transport layer 305 , and an electron injection layer 306 . However, the scope of the present application is not limited by such a laminated structure, and if necessary, the remaining layers except for the light emitting layer may be omitted, and other necessary functional layers may be further added.

The organic material layer including the compound of Formula 1 may further include other materials as needed.

In the organic light emitting device according to an exemplary embodiment of the present application, materials other than the heterocyclic compound of Formula 1 are exemplified below, but these are for illustration only and not for limiting the scope of the present application, may be substituted with known materials.

Materials having a relatively large work function may be used as the anode material, and a transparent conductive oxide, metal, or conductive polymer may be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

Materials having a relatively low work function may be used as the cathode material, and metal, metal oxide, conductive polymer, or the like may be used. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

As the hole injection material, a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or Advanced Material, 6, p.677 (1994). starburst-type amine derivatives such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m- MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), soluble conductive polymers polyaniline/dodecylbenzenesulfonic acid (Polyaniline/Dodecylbenzenesulfonic acid) or poly( 3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/Camphor sulfonic acid or polyaniline/ Poly(4-styrenesulfonate) (Polyaniline/Poly(4-styrene-sulfonate)) and the like may be used.

As the hole transport material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used, and a low molecular weight or high molecular material may be used.

Examples of the electron transport material include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, and fluorenone. Derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, etc. may be used, and polymer materials as well as low molecular weight materials may be used.

As the electron injection material, for example, LiF is typically used in the art, but the present application is not limited thereto.

A red, green or blue light emitting material may be used as the light emitting material, and if necessary, two or more light emitting materials may be mixed and used. In this case, two or more light emitting materials may be deposited and used as separate sources, or may be premixed and deposited as a single source. In addition, although a fluorescent material can be used as a light emitting material, it can also be used as a phosphorescent material. As the light emitting material, a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used, but materials in which the host material and the dopant material together participate in light emission may be used.

When mixing and using the host of the light emitting material, a host of the same series may be mixed and used, or a host of different series may be mixed and used. For example, any two or more types of n-type host material or p-type host material may be selected and used as the host material of the light emitting layer.

The organic light emitting device according to the exemplary embodiment of the present application may be a top emission type, a back emission type, or a double side emission type depending on a material used.

The heterocyclic compound according to an exemplary embodiment of the present application may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, and an organic transistor.

Hereinafter, the present specification will be described in more detail through examples, but these are only for illustrating the present application and not for limiting the scope of the present application.

< manufacturing example 1> Preparation of compound 1 (D)

Preparation of compound 1-1

(3-fluoro-2-methoxyphenyl)boronic acid (27.87g, 164.01mmol), 5-bromo in a 1-neck round bottom flask (One neck rbf) -1-chloro-3-fluoro-2-iodobenzene (5-bromo-1-chloro-3-fluoro-2-iodobenzene) (50 g, 149.10 mmol), tetrakis (triphenylphosphine) palladium (0 ) (Tetrakis(triphenylphosphine)palladium(0)) (8.61g, 7.46mmol), Sodium hydroxide (11.93g, 298.20mmol), 1,4-Dioxane/water (500mL/150mL) mixture of 120 It was refluxed at ℃.

Extracted with dichloromethane (Dichloromethane), dried over _{MgSO 4 .} After silica gel filter, it was concentrated to obtain compound 1-1. (49.24g, 99%)

Preparation of compound 1-2

4'-bromo-2'-chloro-3,6'-difluoro-2-methoxy-1,1'-biphenyl (4'-bromo-2) in a one-necked round bottom flask (one neck rbf) A mixture of '-chloro-3,6'-difluoro-2-methoxy-1,1'-biphenyl) (49.24g, 147.62mmol) and methylene chloride (MC) (500mL) was lowered to 0 °C and BBr ₃ ( 73.96 g, 295.24 mmol) was added dropwise, and the temperature was raised to room temperature (25° C.) and stirred for 3 hours.

The reaction was terminated with distilled water, extracted with dichloromethane, and dried over _{MgSO 4 .} After silica gel filter, it was concentrated to obtain compound 1-2. (44.81 g, 95%)

Preparation of compound 1-3

4'-bromo-2'-chloro-3,6'-difluoro-[1,1'-biphenyl]-2-ol (4'-bromo- 2'-chloro-3,6'-difluoro-[1,1'-biphenyl]-2-ol) (44.81g, 140.24mmol), Cs ₂ CO ₃ (91.39g, 280.48mmol), Dimethylacetamide ) (500 mL) was stirred at 180 °C. After cooling, the filtrate was filtered, and the solvent of the filtrate was removed, followed by column purification to obtain compound 1-3. (36.54 g, 87%)

Preparation of compound 1-4

3-bromo-1-chloro-6-fluorodibenzo [b, d] furan (3-bromo-1-chloro-6-fluorodibenzo [b, d] furan) in a 1-neck round bottom flask (One neck rbf) (36.54g, 122.00mmol), Phenylboronic acid (16.36g, 134.20mmol), Tetrakis(triphenylphosphine)palladium(0)(Tetrakis(triphenylphosphine)palladium(0)) (7.05g, 6.10) mmol), potassium carbonate (33.72 g, 244 mmol), and 1,4-Dioxane/water (360 mL/108 mL) were refluxed at 120 °C.

Extracted with dichloromethane (Dichloromethane), dried over _{MgSO 4 .} Column purification was performed to obtain compound 1-4. (28.96g, 80%)

Preparation of compounds 1-5

1-chloro-6-fluoro-3-phenyldibenzo[b,d]furan in a 1-neck round bottom flask (One neck rbf) (28.96g, 97.60mmol), Bis(pinacolato)diboron) (49.57g, 195.2mmol), Pd ₂ (dba) ₃ (8.94g, 9.76mmol), SPhos (8.01g, 19.52mmol), potassium acetate (28.74g, 29.28mmol), and a mixture of 1,4-Dioxane (290mL) was refluxed at 140°C.

After concentration by extraction with dichloromethane (Dichloromethane), a silica gel filter was applied. After concentration, it was treated with dichloromethane/methanol to obtain compound 1-5. (36.38 g, 96%)

Preparation of compounds 1-6

2-(6-fluoro-3-phenyldibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3 in a 1-neck round bottom flask (one neck rbf) ,2-dioxaborolane (2-(6-fluoro-3-phenyldibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane) ( 36.38 g, 93.70 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (27.59 g, 103.07) mmol), tetrakis (triphenylphosphine) palladium (0) (Tetrakis (triphenylphosphine) palladium (0)) (5.41 g, 4.69 mmol), potassium carbonate (25.73 g, 186.14 mmol), 1,4 -Dioxane/water (930mL/279mL) mixture was refluxed at 120°C.

The solid obtained by vacuum filter was dissolved in dichlorobenzene, filtered through silica gel, and concentrated to obtain compound 1-6. (35.15 g, 76%)

Preparation of compound 1 (D)

2-(6-fluoro-3-phenyldibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-tri in a 1-neck round bottom flask (one neck rbf) Azine (2-(6-fluoro-3-phenyldibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-triazine) (35.15 g, 71.22 mmol), 9H-carbazole A mixture of (9H-carbazole) (13.10 g, 78.34 mmol), Cs ₂ CO ₃ (46.41 g, 142.44 mmol), and dimethylacetamide (350 mL) was stirred at 180°C.

The solid obtained by vacuum filter was dissolved in dichlorobenzene, filtered through silica gel, and concentrated to obtain compound 1 (D). (37.42 g, 82%)

In Preparation Example 1, the target compound D was synthesized in the same manner as in Preparation Example 1, except that intermediates A, B, and C of Table 1 were used.

[ Preparation Example 2 ] Preparation of compound 101 (E)

Preparation of compound 101-1

(4-fluoro-2-methoxyphenyl) boronic acid (27.87 g, 164.01 mmol), 5-bromo in a 1-neck round bottom flask (One neck rbf) -1-chloro-3-fluoro-2-iodobenzene (5-bromo-1-chloro-3-fluoro-2-iodobenzene) (50 g, 149.10 mmol), tetrakis (triphenylphosphine) palladium (0 ) (Tetrakis(triphenylphosphine)palladium(0)) (8.61g, 7.46mmol), Sodium hydroxide (11.93g, 298.20mmol), 1,4-Dioxane/water (500mL/150mL) mixture of 120 It was refluxed at ℃.

Extracted with dichloromethane (Dichloromethane), dried over _{MgSO 4 .} After the silica gel filter, it was concentrated to obtain compound 101-1. (43.27 g, 87%)

Preparation of compound 101-2

4-bromo-2-chloro-4'6,-difluoro-2'-methoxy-1,1'-biphenyl (4-bromo-2-chloro) in a 1-neck round bottom flask (One neck rbf) A mixture of -4',6-difluoro-2'-methoxy-1,1'-biphenyl) (43.27g, 129.72mmol) and methylene chloride (MC) (430mL) was lowered to 0 °C and BBr ₃ (64.99g) , 259.44 mmol) was added dropwise, the temperature was raised to room temperature, and the mixture was stirred for 3 hours.

The reaction was terminated with distilled water, extracted with dichloromethane, and dried over _{MgSO 4 .} After the silica gel filter, it was concentrated to obtain compound 101-2. (40.20g, 97%)

Preparation of compound 101-3

4'-bromo-2'-chloro-4,6'-difluoro-[1,1'-biphenyl]-2-ol (4'-bromo- 2'-chloro-4,6'-difluoro-[1,1'-biphenyl]-2-ol) (40.20g, 134.21mmol), Cs ₂ CO ₃ (87.46g, 268.42mmol), Dimethylacetamide ) (400 mL) was stirred at 180 °C. After cooling, the mixture was filtered, and the solvent of the filtrate was removed and then column purification was performed to obtain compound 101-3. (36.18g, 90%)

Preparation of compound 101-4

3-bromo-1-chloro-7-fluorodibenzo [bd] furan (36.18) in a 1-neck round bottom flask (One neck rbf) g, 120.79 mmol), Phenylboronic acid (16.20 g, 132.87 mmol), tetrakis (triphenylphosphine) palladium (0) (Tetrakis (triphenylphosphine) palladium (0)) (6.98 g, 6.04 mmol) , potassium carbonate (33.39g, 241.58mmol), and 1,4-Dioxane/water (360mL/108mL) mixture was refluxed at 120 ℃.

Extracted with dichloromethane (Dichloromethane), dried over _{MgSO 4 .} Column purification was performed to obtain compound 101-4. (33.69 g, 94%)

Preparation of compound 101-5

1-chloro-7-fluoro-3-phenyldibenzo[b,d]furan in a 1-neck round bottom flask (One neck rbf) (33.69g, 113.54mmol), Bis(pinacolato)diboron) (88.16g, 227.08mmol), Pd ₂ (dba) ₃ (10.40g, 11.35mmol), SPhos (9.32g, 22.71 mmol), potassium acetate (33.43 g, 340.62 mmol), and a mixture of 1,4-dioxane (1,4-Dioxane) (340 mL) was refluxed at 140 °C.

After concentration by extraction with dichloromethane (Dichloromethane), a silica gel filter was applied. After concentration, dichloromethane/Methanol treatment was performed to obtain compound 101-5. (38.79g, 88%)

Preparation of compound 101-6

2-(6-fluoro-3-phenyldibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3 in a 1-neck round bottom flask (one neck rbf) ,2-dioxaborolane (2-(6-fluoro-3-phenyldibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane) ( 38.79 g, 99.91 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (29.42 g, 109.90) mmol), tetrakis (triphenylphosphine) palladium (0) (Tetrakis (triphenylphosphine) palladium (0)) (5.77 g, 5.00 mmol), potassium carbonate (27.62 g, 199.82 mmol), 1,4 -Dioxane/water (380mL/114mL) mixture was refluxed at 120°C.

The solid obtained by vacuum filter was dissolved in dichlorobenzene, filtered through silica gel, and concentrated to obtain compound 101-6. (45.36g, 92%)

Preparation of compound 101 (E)

2-(6-fluoro-3-phenyldibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-tri in a 1-neck round bottom flask (one neck rbf) Azine (2-(6-fluoro-3-phenyldibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-triazine) (45.36g, 91.91mmol), 9H-carbazole A mixture of (9H-carbazole) (16.91 g, 101.10 mmol), Cs ₂ CO ₃ (59.89 g, 183.82 mmol), and dimethylacetamide (450 mL) was stirred at 180°C.

The solid obtained by vacuum filter was dissolved in dichlorobenzene, filtered through silica gel, and concentrated to obtain compound 101 (E). (46.52 g, 79%)

In Preparation Example 2, the target compound E was synthesized in the same manner as in Preparation Example 2, except that intermediates A, B and C of Table 2 were used.

Heterocyclic compounds corresponding to Formula 1 other than the compounds described in Preparation Examples 1 and 2, Tables 1 and 2 were also prepared in the same manner as described in Preparation Examples.

Synthesis confirmation data of the compounds prepared above are as shown in [Table 3] and [Table 4] below.

compound	FD-Mass	compound	FD-Mass
One	m/z = 640.75 (C45H28N4O=640.23)	2	m/z = 740.87 (C53H32N4O=740.26)
3	m/z = 690.81 (C49H30N4O=690.24)	4	m/z = 716.84 (C51H32N4O=716.26)
5	m/z = 716.84 (C51H32N4O=716.26)	6	m/z = 746.89 (C51H30N4OS=746.21)
7	m/z = 746.89 (C51H30N4OS=746.21)	8	m/z = 690.81 (C49H30N4O=690.24)
9	m/z = 730.83 (C51H30N4O2=730.24)	10	m/z = 730.83 (C51H30N4O2=730.24)
11	m/z = 716.84 (C51H32N4O=716.26)	12	m/z = 716.84 (C51H32N4O=716.26)
13	m/z = 716.84 (C51H32N4O=716.26)	14	m/z = 805.94 (C57H35N5O=805.28)
15	m/z = 746.89 (C51H30N4OS=746.21)	16	m/z = 730.83 (C51H30N4O2=730.24)
17	m/z = 716.84 (C51H32N4O=716.26)	18	m/z = 716.84 (C51H32N4O=716.26)
19	m/z = 716.84 (C51H32N4O=716.26)	20	m/z = 601.71 (C43H27N3O=601.22)
21	m/z = 639.76 (C46H29N3O=639.23)	22	m/z = 715.86 (C52H33N3O=715.26)
23	m/z = 715.86 (C52H33N3O=715.26)	24	m/z = 715.86 (C52H33N3O=715.26
25	m/z = 792.94 (C57H36N4O=792.29)	26	m/z = 716.84 (C51H32N4O=716.26)
27	m/z = 805.94 (C57H35N5O=805.28)	28	m/z = 882.04 (C63H39N5O=881.32)
29	m/z = 758.93 (C54H38N4O=758.30)	30	m/z = 756.91 (C54H36N4O=756.29)
31	m/z = 746.89 (C51H30N4OS=746.21)	32	m/z = 730.83 (C51H30N4O2=730.24)
33	m/z = 822.99 (C57H34N4O=822.25)	34	m/z = 690.81 (C49H30N4O=690.24)
35	m/z = 690.81 (C49H30N4O=690.24)	36	m/z = 740.87 (C53H32N4O=740.26)
37	m/z = 739.88 (C54H33N3O=739.26)	38	m/z = 792.94 (C57H36N4O=792.29)
39	m/z = 792.94 (C57H36N4O=792.29)	40	m/z = 791.95 (C58H37N3O=791.29)
41	m/z = 792.94 (C57H36N4O=792.29)	42	m/z = 677.81 (C49H31N3O=677.25)
43	m/z = 766.90 (C55H34N4O=766.27)	44	m/z = 822.99 (C57H34N4OS=822.25)
45	m/z = 822.99 (C57H34N4OS=822.25)	46	m/z = 882.04 (C63H39N5O=881.32)
47	m/z = 783.95 (C55H33N3OS=783.23)	48	m/z = 822.99 (C57H34N4OS=822.25
49	m/z = 783.95 (C55H33N3OS=783.23)	50	m/z = 753.91 (C55H35N3O=753.28)
51	m/z = 783.95 (C55H33N3OS=783.23)	52	m/z = 804.95 (C58H36N4O=804.29)
53	m/z = 796.95 (C55H32N4OS=796.23)	54	m/z = 806.93 (C57H34N4O2=806.27)
55	m/z = 805.94 (C58H35N3O2=805.27)	56	m/z = 804.95 (C58H36N4O=804.29)
57	m/z = 756.91 (C54H36N4O=756.29)	58	m/z = 756.91 (C54H36N4O=756.29)
59	m/z = 793.97 (C58H39N3O=793.31)	60	m/z = 793.97 (C58H39N3O=793.31)
61	m/z = 689.82 (C50H31N3O=689.25)	62	m/z = 765.92 (C56H35N3O=765.28)
63	m/z = 930.12 (C69H43N3O=929.34)	64	m/z = 765.92 (C56H35N3O=765.28)
65	m/z = 778.92 (C56H34N4O=778.27)	66	m/z = 688.83 (C51H32N2O=688.25)
67	m/z = 777.93 (C57H35N3O=777.28)	68	m/z = 765.92 (C51H30N2OS=718.21)
69	m/z = 794.97 (C57H34N2OS=794.24)	70	m/z = 688.83 (C51H32N2O=688.25)
71	m/z = 833.01 (C60H40N4O=832.32)	72	m/z = 881.05 (C64H40N4O=880.32)
73	m/z = 716.84 (C51H32N4O=716.26)	74	m/z = 677.81 (C49H31N3O=677.25)
75	m/z = 792.94 (C57H36N4O=792.29)	76	m/z = 753.91 (C55H35N3O=753.28)
77	m/z = 663.78 (C48H29N3O=663.23)	78	m/z = 739.88 (C54H33N3O=739.26)
79	m/z = 791.95 (C58H37N3O=791.29)	80	m/z = 753.91 (C52H31N3OS=745.22)
81	m/z = 769.92 (C54H31N3OS=969.22)	82	m/z = 688.83 (C51H32N2O=688.25)
83	m/z = 753.91 (C55H35N3O=753.28)	84	m/z = 783.95 (C55H33N3OS=783.23)
85	m/z = 846.02 (C60H35N3OS=845.25)	86	m/z = 846.02 (C60H35N3OS=845.25)
87	m/z = 791.95 (C58H37N3O=791.29)	88	m/z = 791.95 (C58H37N3O=791.29)
89	m/z = 822.00 (C58H35N3OS=821.25)	90	m/z = 822.00 (C58H35N3OS=821.25)
91	m/z = 822.00 (C58H35N3OS=821.25)	92	m/z = 764.93 (C57H36N2O=764.28)
93	m/z = 792.94 (C57H36N4O=792.29)	94	m/z = 893.06 (C65H40N4O=892.32)
95	m/z = 945.14 (C69H44N4O=944.35)	96	m/z = 873.05 (C61H36N4OS=872.26)
97	m/z = 931.11 (C68H42N4O=930.34)	98	m/z = 753.91 (C55H35N3O=753.28)
99	m/z = 860.05 (C61H37N3OS=859.27)	100	m/z = 860.05 (C61H37N3OS=859.27)
101	m/z = 640.75 (C45H26N4O=640.23)	102	m/z = 740.87 (C53H32N4O=740.26)
103	m/z = 690.81 (C51H30N4OS=690.24)	104	m/z = 716.84 (C51H32N4O=716.26)
105	m/z = 730.83 (C51H32N4O=716.26)	106	m/z = 746.89 (C51H30N4OS=746.21)
107	m/z = 746.89 (C51H30N4OS=746.21)	108	m/z = 690.81 (C51H32N4O=690.24)
109	m/z = 730.83 (C51H30N4O2=730.24)	110	m/z = 730.83 (C51H30N4O2=730.24)
111	m/z = 716.84 (C51H32N4O=716.26)	112	m/z = 716.84 (C51HH32N4O=716.26)
113	m/z = 716.84 (C51H32N4O=716.26)	114	m/z = 805.94 (C57H35N5O=805.28)
115	m/z = 746.89 (C51H30N4OS=746.21)	116	m/z = 730.83 (C51H30N4O2=730.24)
117	m/z = 716.84 (C51H32N4O=716.26)	118	m/z = 716.84 (C51H32N4O=716.26)
119	m/z = 716.84 (C51H32N4O=716.26)	120	m/z = 601.71 (C43H27N3O=601.22)
121	m/z = 639.76 (C46H29N3O=639.23)	122	m/z = 715.86 (C52H33N3O=715.26)
123	m/z = 715.86 (C52H33N3O=715.26)	124	m/z = 715.86 (C52H33N3O=715.26
125	m/z = 792.94 (C57H36N4O=792.29)	126	m/z = 716.84 (C51H32N4O=716.26)
127	m/z = 805.94 (C57H35N5O=805.28)	128	m/z = 882.04 (C63H39N5O=881.32)
129	m/z = 758.93 (C54H38N4O=758.30)	130	m/z = 756.91 (C54H36N4O=756.29)
131	m/z = 746.89 (C51H30N4OS=746.21)	132	m/z = 730.83 (C51H30N4O2=730.24)
133	m/z = 822.99 (C57H34N4O=822.25)	134	m/z = 690.81 (C49H30N4O=690.24)
135	m/z = 690.81 (C49H30N4O=690.24)	136	m/z = 740.87 (C53H32N4O=740.26)
137	m/z = 739.88 (C54H33N3O=739.26)	138	m/z = 792.94 (C57H36N4O=792.29)
139	m/z = 792.94 (C57H36N4O=792.29)	140	m/z = 791.95 (C58H37N3O=791.29)
141	m/z = 792.94 (C57H36N4O=792.29)	142	m/z = 677.81 (C49H31N3O=677.25)
143	m/z = 766.90 (C55H34N4O=766.27)	144	m/z = 822.99 (C57H34N4OS=822.25)
145	m/z = 822.99 (C57H34N4OS=822.25)	146	m/z = 882.04 (C63H39N5O=881.32)
147	m/z = 783.95 (C55H33N3OS=783.23)	148	m/z = 822.99 (C57H34N4OS=822.25
149	m/z = 783.95 (C55H33N3OS=783.23)	150	m/z = 753.91 (C55H35N3O=753.28)
151	m/z = 783.95 (C55H33N3OS=783.23)	152	m/z = 804.95 (C58H36N4O=804.29)
153	m/z = 796.95 (C55H32N4OS=796.23)	154	m/z = 806.93 (C57H34N4O2=806.27)
155	m/z = 805.94 (C58H35N3O2=805.27)	156	m/z = 804.95 (C58H36N4O=804.29)
157	m/z = 756.91 (C54H36N4O=756.29)	158	m/z = 756.91 (C54H36N4O=756.29)
159	m/z = 793.97 (C58H39N3O=793.31)	160	m/z = 793.97 (C58H39N3O=793.31)
161	m/z = 689.82 (C50H31N3O=689.25)	162	m/z = 765.92 (C56H35N3O=765.28)
163	m/z = 930.12 (C69H43N3O=929.34)	164	m/z = 765.92 (C56H35N3O=765.28)
165	m/z = 778.92 (C56H34N4O=778.27)	166	m/z = 688.83 (C51H32N2O=688.25)
167	m/z = 777.93 (C57H35N3O=777.28)	168	m/z = 765.92 (C51H30N2OS=718.21)
169	m/z = 794.97 (C57H34N2OS=794.24)	170	m/z = 688.83 (C51H32N2O=688.25)
171	m/z = 833.01 (C60H40N4O=832.32)	172	m/z = 881.05 (C64H40N4O=880.32)
173	m/z = 716.84 (C51H32N4O=716.26)	174	m/z = 677.81 (C49H31N3O=677.25)
175	m/z = 792.94 (C57H36N4O=792.29)	176	m/z = 753.91 (C55H35N3O=753.28)
177	m/z = 663.78 (C48H29N3O=663.23)	178	m/z = 739.88 (C54H33N3O=739.26)
179	m/z = 791.95 (C58H37N3O=791.29)	180	m/z = 753.91 (C52H31N3OS=745.22)
181	m/z = 769.92 (C54H31N3OS=969.22)	182	m/z = 688.83 (C51H32N2O=688.25)
183	m/z = 753.91 (C55H35N3O=753.28)	184	m/z = 783.95 (C55H33N3OS=783.23)
185	m/z = 846.02 (C60H35N3OS=845.25)	186	m/z = 846.02 (C60H35N3OS=845.25)
187	m/z = 791.95 (C58H37N3O=791.29)	188	m/z = 791.95 (C58H37N3O=791.29)
189	m/z = 822.00 (C58H35N3OS=821.25)	190	m/z = 822.00 (C58H35N3OS=821.25)
191	m/z = 822.00 (C58H35N3OS=821.25)	192	m/z = 764.93 (C57H36N2O=764.28)
193	m/z = 792.94 (C57H36N4O=792.29)	194	m/z = 893.06 (C65H40N4O=892.32)
195	m/z = 945.14 (C69H44N4O=944.35)	196	m/z = 873.05 (C61H36N4OS=872.26)
197	m/z = 931.11 (C68H42N4O=930.34)	198	m/z = 753.91 (C55H35N3O=753.28)
199	m/z = 860.05 (C61H37N3OS=859.27)	200	m/z = 860.05 (C61H37N3OS=859.27)
201	m/z = 746.89 (C51H30N4OS=746.21)	202	m/z = 822.99 (C57H34N4OS=822.25)
203	m/z= 853.03 (C57H32N4OS2=852.20)	204	m/z = 929.13 (C63H36N4OS2 = 928.23)
205	m/z = 806.93 (C57H34N4O2=806.27)	206	m/z = 913.07 (C63H36N4O2S=912.26)
207	m/z = 783.95 (C55H33N3OS=783.23)	208	m/z=987.19 (C70H42N4OS=986.31)
209	m/z = 746.89 (C51H30N4OS=746.21)	210	m/z = 822.99 (C57H34N4OS=822.25)
211	m/z= 853.03 (C57H32N4OS2=852.20)	212	m/z = 929.13 (C63H36N4OS2 = 928.23)
213	m/z = 806.93 (C57H34N4O2=806.27)	214	m/z = 913.07 (C63H36N4O2S=912.26)
215	m/z = 783.95 (C55H33N3OS=783.23)	216	m/z=987.19 (C70H42N4OS=986.31)

compound	1 H NMR (CDCl 3 , 200 Mz)
One	δ = 8.55 (1H, d), 8.36 (4H, m), 8.19 (1H, d), 7.94 (2H, d), 7.75 to 7.86 (4H, m), 7.31 to 7.58 (14H, m), 7.16 to 7.20 (2H, m)
4	δ = 8.55 (1H, d), 8.36 (4H, m), 7.75 to 7.99 (11H, m), 7.31 to 7.50 (15H, m), 7.16 (1H, t)
5	δ = 8.55 (1H, d), 8.31~8.36 (5H, m), 7.86~7.94 (4H, m), 7.74~7.81 (6H, m), 7.31~7.50 (15H, m), 7.16 (1H, t) )
6	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 7.93 to 7.94 (3H, d), 7.75 to 7.86 (6H, m), 7.31 to 7.56 (14H, m), 7.16 (1H, t)
7	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 8.05 (1H, d), 7.93 to 7.94 (3H, d), 7.86 (1H, s), 7.75 to 7.81 ( 3H, m), 7.31~7.60 (15H, m), 7.16 (1H, t)
9	δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 to 7.98 (3H, m), 7.75 to 7.86 (5H, m), 7.31 to 7.54 (16H, m), 7.16 (1H, t)
10	δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 to 7.98 (3H, m), 7.86 (1H, d), 7.75 to 7.81 (3H, m), 7.31 to 7.54 (17H, m), 7.16 (1H, t)
14	δ = 8.55 (1H, d), 8.36 (4H, m), 8.19 (1H, d), 7.94 (2H, d), 7.86 (1H, s), 7.75 to 7.81 (3H, m), 7.31 to 7.62 ( 20H, m), 7.16~7.20 (2H, m)
16	δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 to 7.98 (3H, m), 7.86 (1H, s), 7.75 to 7.81 (3H, m), 7.31 to 7.54 (17H, m), 7.16 (1H, t)
22	δ = 8.55 (1H, d), 8.19~8.23 (2H, m), 7.94 (6H, m), 7.73~7.86 (7H, m), 7.31~7.61 (15H, m), 7.16~7.20 (2H, m) )
25	δ = 8.62 (1H, d), 8.31 to 8.36 (4H, m), 8.22 (1H, d), 7.86 to 7.94 (3H, m), 7.74 to 7.81 (9H, m), 7.41 to 7.50 (16H, m) ), 7.31 (1H, d)
27	δ = 8.55 (2H, d), 8.36 (4H, m), 8.12 (1H, d), 7.94 (3H, d), 7.86 (1H, s), 7.75 to 7.81 (3H, m), 7.31 to 7.62 ( 19H, m), 7.16 (2H, t)
29	δ = 8.55 (1H, d), 8.36 (4H, m), 8.23 (1H, s), 7.94 (2H, d), 7.75 to 7.86 (4H, m), 7.29 to 7.50 (14H, m), 7.16 ( 1H, t), 6.64 (1H, m), 5.80 (2H, m), 3.62 (1H, t), 2.55 (1H, t), 1.35 (6H, s)
31	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 8.05 (1H, d), 93 to 7.94 (3H, m), 7.86 (1H, s), 7.75 to 7.81 ( 3H, m), 7.31~7.56 (16H, m), 7.16 (1H, t)
33	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 8.17 to 8.24 (3H, m), 7.75 to 7.99 (10H, m), 7.31 to 7.56 (14H, m), 7.16 (1H, t)
38	δ = 8.55 (1H, d), 8.19 (1H, d), 7.94 to 7.96 (6H, m), 7.75 to 7.86 (8H, m), 7.16 to 7.58 (20H, m)
44	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 7.93 to 7.96 (5H, m), 7.75 to 7.86 (8H, m), 7.25 to 7.56 (16H, m), 7.16 (1H, t)
46	δ = 8.55 (1H, d), 8.36 to 8.38 (5H, m), 8.19 (1H, d), 7.94 (3H, m), 7.86 (1H, s), 7.73 to 7.81 (4H, m), 7.31 to 7.62 (22H, m), 7.16~7.20 (2H, m)
48	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 8.12 (2H, m), 7.68 to 7.99 (10H, m), 7.31 to 7.56 (15H, m), 7.16 ( 1H, t)
54	δ = 8.55 (1H, d), 8.36 (4H, m), 7.75 to 8.03 (13H, m), 7.31 to 7.54 (15H, m), 7.16 (1H, t)
58	δ = 8.55 (1H, d), 8.36 (4H, m), 8.21 to 8.24 (2H, m), 7.74 to 7.94 (8H, m), 7.31 to 7.57 (14H, m), 7.16 (1H, t), 1.69 (6H, s)
64	δ = 8.55 (1H, d), 8.30 to 8.31 (3H, m), 8.13 (1H, d), 7.74 to 7.94 (16H, m), 7.35 to 7.58 (13H, m), 7.16 (1H, t)
66	δ = 8.55 (1H, d), 8.29 (2H, m), 8.18 to 8.19 (2H, m), 7.31 to 7.99 (24H, m), 7.15 to 7.20 (3H, m)
68	δ = 8.55 (1H, d), 8.45 (1H, d), 8.29 (2H, d), 8.18 (1H, d), 7.31 to 7.99 (23H, m), 7.15 to 7.16 (2H, m)
71	δ = 8.55 (1H, d), 8.36 (2H, m), 8.21 to 8.24 (2H, m), 7.74 to 7.96 (12H, m), 7.25 to 7.57 (16H, m), 7.16 (1H, t), 1.69 (6H, s)
73	δ = 8.55 (1H, d), 8.36 (4H, m), 8.19 to 8.21 (2H, m), 8.02 to 8.08 (2H, m), 7.94 (1H, d), 7.86 (1H, s), 7.75 to 7.68 (4H, m), 7.35~7.60 (15H, m), 7.16~7.20 (2H, m)
83	δ = 8.55~8.56 (2H, m), 8.31~8.38 (2H, m), 7.73~7.94 (13H, m), 7.28~7.49 (17H, m), 7.16 (1H, t)
86	δ = 8.87 (1H, d), 8.55 (1H, d), 8.45 (1H, d), 8.14 to 8.26 (7H, m), 7.75 to 7.99 (10H, m), 7.31 to 7.56 (13H, m), 7.15~7.16 (2H, m)
90	δ = 8.55 (1H, d), 8.45 (1H, d), 8.35 (2H, m), 7.93 to 7.94 (3H, m), 7.75 to 7.86 (10H, m), 7.31 to 7.65 (17H, m), 7.16 (1H, t)
92	δ = 8.39 (1H, d), 8.27 to 8.30 (2H, m), 8.08 to 8.18 (3H, m),
96	δ = 8.39 (1H, d), 8.27 to 8.03 (2H, m), 8.08 to 8.18 (3H, m), 7.75 to 7.99 (16H, m), 7.41 to 7.49 (13H, m), 7.31 (1H, d) )
100	δ = 8.55~8.56 (2H, m), 8.45 (1H, d), 8.05 (1H, d), 7.73~7.96 (12H, m), 7.25~7.61 (20H, m), 7.16 (1H, t)
101	δ = 8.55 (1H, d), 8.36 (4H, m), 8.19 (1H, d), 7.94 to 7.98 (2H, m), 7.75 to 7.86 (4H, m), 7.35 to 7.58 (13H, m), 7.16~7.25 (3H, m)
103	δ = 8.55 (1H, d), 8.28~8.36 (5H, m), 8.11 (1H, d), 7.94~7.98 (2H, m), 7.69~7.86 (6H, m), 7.35~7.55 (13H, m) ), 7.25 (1H, d), 7.16 (1H, t)
104	δ = 8.55 (1H, d), 8.36 (4H, m), 7.75 to 7.99 (11H, m), 7.35 to 7.54 (14H, m), 7.25 (1H, d), 7.16 (1H, t)
106	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 7.93 to 7.98 (3H, m), 7.75 to 7.86 (6H, m), 7.41 to 7.56 (13H, m), 7.25 (1H, d), 7.16 (1H, t)
109	δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 to 7.98 (3H, m), 7.75 to 7.86 (5H, m), 7.25 to 7.54 (16H, m), 7.16 (1H, t)
110	δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 to 7.98 (3H, m), 7.86 (1H, s), 7.75 to 7.81 (3H, m), 7.25 to 7.54 (17H, m), 7.16 (1H, t)
112	δ = 8.55 (1H, d), 8.36 (4H, m), 8.19 (1H, d), 7.94 to 7.98 (3H, m), 7.73 to 7.86 (5H, m), 7.35 to 7.61 (15H, m), 7.16~7.25 (3H, m)
114	δ = 8.55 (1H, d), 8.36 (4H, m), 8.19 (1H, d), 7.94 to 7.98 (2H, m), 7.86 (1H, s), 7.75 to 7.81 (3H, m), 7.35 to 7.62 (20H, m), 7.16~7.25 (3H, m)
116	δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 to 7.98 (3H, m), 7.86 (1H, s), 7.75 to 7.81 (3H, m), 7.25 to 7.54 (17H, m), 7.16 (1H, t)
117	δ = 8.55 (1H, d), 8.36~8.38 (5H, m), 8.19 (1H, d), 7.94~7.98 (3H, m), 7.73~7.86 (5H, m), 7.35~7.61 (14H, m) ), 7.16~7.25 (3H, m)
120	δ = 8.55 (1H, m), 8.19 (1H, d), 7.94 to 7.98 (2H, m), 7.75 to 7.86 (5H, m), 7.16 to 7.58 (17H, m)
123	δ = 8.55 (1H, d), 8.23 (1H, d), 8.19~8.23 (2H, m), 7.94~7.98 (7H, m), 7.73~7.86 (5H, m), 7.35~7.58 (14H, m) ), 7.16~7.25 (3H, m)
127	δ = 8.55 (2H, d), 8.36 (4H, m), 8.12 (1H, d), 7.94 to 7.98 (3H, m), 7.86 (1H, s), 7.75 to 7.81 (3H, m), 7.35 to 7.62 (18H, m), 7.25 (1H, d), 7.16 (2H, t)
129	δ = 8.55 (1H, d), 8.36 (4H, m), 8.23 (1H, s), 7.94 to 7.98 (2H, m), 7.75 to 7.86 (4H, m), 7.25 to 7.54 (14H, m), 7.16 (1H, t), 6.64 (1H, m), 5.80 (2H, m), 3.62 (1H, t), 2.55 (1H, t), 1.35 (6H, s)
131	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 8.05 (1H, d), 7.93 to 7.98 (3H, m), 7.75 to 7.86 (4H, m), 7.33 to 7.56 (14H, m), 7.25 (1H, d), 7.16 (1H, t)
133	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 8.17 to 8.24 (3H, m), 7.75 to 7.99 (10H, m), 7.35 to 7.56 (13H, m), 7.25 (1H, d), 7.16 (1H, t)
135	δ = 9.09 (1H, s), 8.49 to 8.55 (2H, m), 8.36 (2H, m), 8.16 to 8.19 (2H, m), 7.94 to 8.00 (4H, m), 7.75 to 7.86 (4H, m) ), 7.35~7.61 (12H, m), 7.16~7.25 (3H, m)
139	δ = 8.55 (1H, d), 8.36 to 8.38 (3H, m), 7.73 to 7.99 (15H, m), 7.16 (1H, d), 7.35 to 7.54 (14H, m), 7.25 (1H, d), 7.16 (1H, t)
142	δ = 8.55~8.56(2H, m), 7.75~7.99 (12H, m), 7.25~7.62 (16H, m), 7.16 (1H, t)
144	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 7.93 to 7.98 (5H, m), 7.75 to 7.86 (8H, m), 7.35 to 7.56 (13H, m), 7.25 (3H, d), 7.16 (1H, t)
145	δ = 8.55 (1H, d), 8.36 to 8.45 (6H, m), 8.05 (1H, d), 7.93 to 7.98 (4H, m), 7.73 to 7.86 (5H, m), 7.35 to 7.61 (15H, m) ), 7.25 (1H, d), 7.16 (1H, t)
146	δ = 8.55 (1H, d), 8.36 to 8.38 (5H, m), 8.19 (1H, d), 7.94 to 7.98 (3H, m), 7.86 (1H, s), 7.73 to 7.81 (4H, m), 7.40~7.58 (21H, m), 7.16~7.25 (3H, m)
151	δ = 8.55 (1H, m), 8.45 (1H, d), 8.09 (1H, s), 7.93 to 7.98 (3H, m), 7.75 to 7.86 (9H, m), 7.25 to 7.56 (16H, m), 7.16 (1H, t)
156	δ = 8.55 (2H, d), 8.23 (1H, s), 8.12 (1H, d), 7.94 to 7.98 (7H, m), 7.75 to 7.86 (4H, m), 7.35 to 7.62 (17H, m), 7.16~7.25 (4H, m)
157	δ = 8.55 (1H, d), 8.36 (4H, m), 8.24 (1H, d), 7.94 to 7.98 (3H, m), 7.67 to 7.86 (6H, m), 7.35 to 7.57 (13H, m), 7.25 (1H, d), 7.16 (1H, t), 1.69 (6H, s)
160	δ = 8.55~8.56 (2H, m), 8.21~8.24 (2H, m), 7.74~7.98 (15H, m), 7.25~7.57 (13H, m), 7.16 (1H, t), 1.69 (6H, s) )
163	δ = 8.55 (1H, d), 8.24 to 8.30 (4H, m), 8.13 (1H, d), 7.94 to 7.98 (2H, m), 7.73 to 7.86 (12H, m), 7.10 to 7.58 (23H, m) )
165	δ = 8.55 (1H, d), 8.13 to 8.19 (2H, m), 7.94 to 7.98 (2H, m), 7.75 to 7.86 (8H, m), 7.35 to 7.65 (18H, m), 7.16 to 7.25 (3H) , m)
168	δ = 8.55 (1H, d), 8.45 (1H, d), 8.29 (2H, d), 8.18 (1H, d), 7.35 to 7.99 (22H, m), 7.25 (1H, d), 7.15 to 7.16 ( 2H, m)
171	δ = 8.55 (1H, d), 8.36 (2H, m), 8.21 to 8.24 (2H, m), 7.74 to 7.98 (12H, m), 7.35 to 7.57 (13H, m), 7.25 (3H, d), 7.16 (1H, t), 1.69 (6H, s)
176	δ = 8.55 (1H, m), 8.19~8.21 (2H, m), 8.03 (1H, d), 7.94 (1H, d), 7.16~7.86 (29H, m)
177	δ = 8.87 (1H, d), 8.71 (1H, d), 8.55 (1H, d), 8.33 (2H, d), 8.19 to 8.20 (2H, d), 7.75 to 7.98 (7H, m), 7.15 to 7.58 (15H, m)
184	δ = 8.55~8.56 (2H, d), 8.38~8.45 (2H, m), 7.73~8.05 (11H, m), 7.25~7.61 (17H, m), 7.16 (1H, t)
188	δ = 8.55 (1H, d), 8.35 (2H, m), 8.19 to 8.21 (2H, m), 8.03 (1H, d), 7.94 (1H, d), 7.35 to 7.86 (28H, m), 7.16 to 7.20 (2H, m)
190	δ = 8.55 (1H, d), 8.45 (1H, d), 8.35 (2H, m), 7.93 to 7.98 (3H, m), 7.75 to 7.86 (10H, m), 7.35 to 7.65 (16H, m), 7.25 (1H, d), 7.16 (1H, t)
195	δ = 8.30~8.38 (4H, m), 8.13 (1H, d), 7.86~7.98 (6H, m), 7.73~7.81 (14H, m), 7.61 (2H, d), 7.41~7.54 (16H, m) ), 7.25 (1H, d)
200	δ = 8.55~8.56 (2H, d), 8.45 (1H, d), 7.73~8.05 (13H, m), 7.16~7.61 (21H, m)
201	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 8.17 to 8.24 (4H, m), 7.93 to 7.98 (3H, m), 7.81 to 7.86 (2H, m), 7.49~7.56 (11H, m), 7.35 (1H, t), 7.16~7.25 (3H, m)
204	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 8.12 to 8.24 (5H, m), 7.93 to 8.05 (5H, m), 7.75 to 7.86 (4H, m), 7.35~7.60 (14H, m), 7.25 (1H, d), 7.16 (1H, t)
205	δ = 8.55 (1H, d), 8.36 (4H, m), 7.75 to 7.99 (13H, m), 7.25 to 7.54 (15H, m), 7.16 (1H, t)
210	δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 8.12 (2H, m), 7.75 to 7.99 (11H, m), 7.31 to 7.56 (14H, m), 7.16 ( 1H, t)
211	δ = 8.55 (1H, d), 8.45 (2H, d), 8.36 (4H, m), 8.17 to 8.24 (3H, m), 8.05 (1H, d), 7.93 to 7.94 (4H, m), 7.81 to 7.86 (2H, m), 7.46~7.60 (12H, m), 7.31~7.35 (2H, m), 7.16 (1H, t)
213	δ = 8.55 (1H, d), 8.36 (4H, m), 7.75 to 7.99 (13H, m), 7.31 to 7.50 (15H, m), 7.16 (1H, t)
215	δ = 8.55~8.56 (2H, m), 8.45 (1H, d), 8.31 (1H, d), 8.12 (2H, m), 7.74~7.99 (11H, m), 7.31~7.62 (15H, m), 7.16 (1H, t)

< Experimental example 1>- Fabrication of organic light emitting device

1) Fabrication of an organic light emitting device

A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and then UVO-treated for 5 minutes using UV in a UV washer. After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and the substrate was transferred to a thermal deposition equipment for organic deposition.

A hole injection layer 2-TNATA (4,4'-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-diphenyl-(1, 1'-biphenyl) -4,4'-diamine) was formed.

A light emitting layer was deposited thereon by thermal vacuum deposition as follows. _{The emission layer was deposited by doping the host with 7% Ir(ppy) 3} using the compounds shown in Table 5 below as a host and Ir(ppy) ₃ (tris(2-phenylpyridine)iridium) as a green phosphorescent dopant, followed by deposition of 400 Å. After that, 60 Å of BCP was deposited as a hole blocking layer, and 200 Å _{of Alq 3 was deposited thereon as an electron transport layer.} Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1200 Å on the electron injection layer to form a negative electrode, thereby forming an organic electric field. A light emitting device was manufactured.

Meanwhile, all organic compounds required for OLED device fabrication ^{were vacuum sublimated and purified under 10 -6} to 10 ^-8 torr for each material, respectively, and used for OLED fabrication.

2) organic electric field Driving voltage and luminous efficiency of light emitting devices

For the organic electroluminescent device manufactured as described above, electroluminescence (EL) characteristics were measured with M7000 of McScience, and the reference luminance was 6,000 through the life equipment measuring device (M6000) manufactured by McScience with the measurement result. At cd/m ² , T ₉₀ was measured. Table 5 shows the characteristics of the organic electroluminescent device of the present invention.

	compound	drive voltage (V)	efficiency (cd/A)	color coordinates (x, y)	life span (T 90 )
Comparative Example 1	A	5.72	45.7	(0.273, 0.687)	54
Comparative Example 2	B	5.53	49.2	(0.275, 0.674)	61
Comparative Example 3	C	5.33	56.5	(0.270, 0.685)	46
Comparative Example 4	D	5.62	47.2	(0.276, 0.681)	53
Comparative Example 5	E	6.01	30.4	(0.271, 0.684)	32
Comparative Example 6	F	5.65	55.1	(0.280, 0.671)	50
Comparative Example 7	G	5.23	56.0	(0.274, 0.672)	65
Comparative Example 8	H	5.29	57.0	(0.279, 0.673)	63
Comparative Example 9	I	5.70	50.5	(0.281, 0.664)	55
Comparative Example 10	J	5.43	48.2	(0.278, 0.677)	51
Comparative Example 11	K	5.69	46.0	(0.286, 0.681)	54
Comparative Example 12	L	7.02	32.4	(0.273, 0.671)	30
Example 1	One	3.70	70.8	(0.278, 0.686)	135
Example 2	4	4.12	73.5	(0.276, 0.680)	126
Example 3	5	5.20	80.5	(0.271, 0.684)	147
Example 4	6	4.55	80.4	(0.279, 0.683)	150
Example 5	7	5.12	76.1	(0.274, 0.667)	136
Example 6	9	4.09	77.0	(0.287, 0.674)	144
Example 7	10	3.74	74.2	(0.283, 0.677)	130
Example 8	14	3.89	79.6	(0.279, 0.676)	149
Example 9	16	4.14	80.3	(0.272, 0.679)	135
Example 10	22	3.98	76.7	(0.273, 0.671)	133
Example 11	25	3.77	74.4	(0.271, 0.678)	147
Example 12	27	3.86	70.9	(0.279, 0.675)	146
Example 13	29	3.74	71.6	(0.287, 0.673)	144
Example 14	31	3.88	76.5	(0.271, 0.672)	141
Example 15	33	3.89	80.4	(0.288, 0.680)	150
Example 16	38	3.73	77.6	(0.286, 0.681)	143
Example 17	44	4.86	75.6	(0.274, 0.678)	131
Example 18	46	4.90	74.9	(0.274, 0.677)	129
Example 19	48	5.17	79.9	(0.278, 0.679)	147
Example 20	54	4.63	74.5	(0.270, 0.674)	127
Example 21	58	5.17	80.4	(0.271, 0.687)	143
Example 22	64	4.69	79.2	(0.284, 0.683)	144
Example 23	66	3.80	77.1	(0.283, 0.680)	141
Example 24	68	4.76	74.2	(0.279, 0.688)	131
Example 25	71	4.85	76.8	(0.285, 0.669)	139
Example 26	73	5.14	77.5	(0.281, 0.676)	134
Example 27	83	3.89	76.1	(0.277, 0.682)	148
Example 28	86	3.79	75.3	(0.288, 0.682)	130
Example 29	90	3.88	78.0	(0.274, 0.672)	125
Example 30	92	4.15	71.8	(0.276, 0.674)	127
Example 31	96	4.53	77.6	(0.275, 0.673)	126
Example 32	100	4.73	80.4	(0.279, 0.674)	136
Example 33	101	3.60	57.6	(0.278, 0.677)	148
Example 34	103	5.10	70.4	(0.280, 0.675)	174
Example 35	104	3.69	59.5	(0.273, 0.670)	169
Example 36	106	3.89	69.7	(0.270, 0.668)	175
Example 37	109	3.61	66.5	(0.271, 0.663)	166
Example 38	110	4.84	61.7	(0.274, 0.681)	163
Example 39	112	4.44	78.5	(0.272, 0.666)	171
Example 40	114	5.06	66.5	(0.273, 0.665)	173
Example 41	116	3.82	61.1	(0.271, 0.660)	159
Example 42	117	3.94	62.8	(0.263, 0.671)	168
Example 43	123	4.09	68.5	(0.280, 0.683)	166
Example 44	127	4.18	63.8	(0.277, 0.679)	167
Example 45	129	5.04	69.4	(0.278, 0.679)	159
Example 46	131	3.84	58.8	(0.274, 0.680)	174
Example 47	133	4.06	57.6	(0.279, 0.677)	166
Example 48	135	3.69	62.2	(0.280, 0.686)	167
Example 49	139	4.14	63.8	(0.283, 0.681)	169
Example 50	142	4.48	67.0	(0.287, 0.685)	170
Example 51	144	4.02	67.2	(0.284, 0.681)	173
Example 52	145	4.53	69.8	(0.285, 0.680)	155
Example 53	146	4.87	64.8	(0.284, 0.677)	159
Example 54	151	4.94	64.0	(0.277, 0.680)	169
Example 55	156	3.86	66.7	(0.278, 0.673)	167
Example 56	157	3.74	69.2	(0.280, 0.672)	166
Example 57	160	3.86	64.0	(0.279, 0.675)	173
Example 58	163	3.78	67.4	(0.289, 0.674)	170
Example 59	165	3.71	68.5	(0.271, 0.675)	177
Example 60	168	3.64	66.8	(0.270, 0.672)	168
Example 61	171	5.05	67.5	(0.277, 0.671)	164
Example 62	176	4.31	68.7	(0.273, 0.677)	154
Example 63	177	4.49	68.7	(0.274, 0.674)	159
Example 64	184	4.07	69.0	(0.270, 0.671)	168
Example 65	188	4.18	57.9	(0.280, 0.670)	173
Example 66	190	4.48	59.4	(0.289, 0.669)	151
Example 67	195	4.69	58.1	(0.279, 0.670)	168
Example 68	200	5.08	59.2	(0.289, 0.667)	157
Example 69	210	5.14	70.5	(0.278, 0.674)	131
Example 70	211	4.97	75.9	(0.275, 0.673)	139
Example 71	213	3.85	74.4	(0.274, 0.687)	141
Example 72	215	3.60	78.6	(0.281, 0.683)	146

As can be seen in Table 5, the heterocyclic compound according to the present application has specific substituents at positions 1 and 3 of one benzene ring of dibenzofuran, and has a carbazole-based substituent on the other benzene ring. In the case of an organic light emitting device including this, it was confirmed that the lifespan and efficiency were excellent.

The substituent of carbazoles substituted on one benzene ring of dibenzofuran according to the present application is a substituent having hole transport characteristics, and N- substituted at position 1 of the other benzene ring of dibenzofuran Het is a substituent having an electron transport characteristic (Electron transport character moiety), and is further characterized as a trisubstituted compound having a substituent of Ar at the 3-position. That is, when Ar is not substituted, the 3rd position of dibenzofuran is relatively short of electrons, and as the 3rd position of dibenzofuran forms a substituent of Ar as shown in Formula 1 of the present application, electrons are abundant As a result, it was confirmed that the stability of the structure was increased, and consequently, the lifespan and current flow of the organic light-emitting device including the same were improved.

As can be seen from Table 5, Comparative Examples 1 to 6 include a heterocyclic compound in which at least one of a carbazole-based substituent/Ar/N-Het is not provided in dibenzofuran, and in this case, three types of dibenzofuran It can be confirmed that the molecular weight is smaller than that of the compound to which the substituent of the compound is bonded, and thus the Td (95%) value is low, and thus the lifespan is poor due to the relatively poor thermal stability.

In particular, oxygen of dibenzofuran has a property of attracting electrons of adjacent carbons because of its greater electronegativity than carbon, and due to this property, the 4th position of dibenzofuran is relatively lacking in electrons than other positions. Accordingly, it was confirmed that when the carbazole-based substituent is bonded to the 4th position, which is a position relatively lacking in electrons, than the 1st or 2nd position of dibenzofuran, the material is structurally much more stable.

In addition, as shown in Formula 1 according to the present application, it is characterized in that it has N-Het substituted at the 1st position of the benzene ring. Dibenzofuran has different electron density at each position due to resonance, and the 1st position of dibenzofuran is more positively charged than 2nd and 4th positions due to resonance. Therefore, it was confirmed that when N-Het having electron transport ability was bonded to position 1 having a relatively positive charge in dibenzofuran, the material was structurally more stable.

In addition, N-carbazole such as Formula 1 of the present application substituted for dibenzofuran may directly transfer the lone pair electrons possessed by nitrogen to the dibenzofuran core by resonance. Accordingly, it was confirmed that the case of having an N-carbazole substituent had better electron transport ability than the case of having a carbazole group substituted with a phenyl group (connected to the carbon of the carbazole) (Comparative Examples 4 and 6 to 9).

In addition, the thermal decomposition temperature (Dissociation temperature (T _d )) values according to the compounds were compared and shown in Table 6 below. Td (95%) values measured by thermogravimetric analysis are shown in Table 6 below.

	compound	T d (95%) (℃)
Comparative Example 1-1	A1	420
Comparative Example 2-1	B1	427
Example 1	One	450
Example 2	4	478
Example 3	5	459
Example 4	6	475
Example 5	7	461
Example 6	9	470
Example 7	10	475
Example 8	14	481
Example 9	16	445
Example 10	22	465
Example 11	25	473
Example 12	27	462
Example 13	29	463
Example 14	31	453
Example 15	33	473
Example 16	38	470
Example 17	44	488
Example 18	46	459
Example 19	48	476
Example 20	54	498
Example 21	58	449
Example 22	64	471
Example 23	66	465
Example 24	68	473
Example 25	71	449
Example 26	73	481
Example 27	83	475
Example 28	86	480
Example 29	90	476
Example 30	92	452
Example 31	96	463
Example 32	100	452
Example 33	101	455
Example 34	103	459
Example 35	104	463
Example 36	106	477
Example 37	109	453
Example 38	110	472
Example 39	112	458
Example 40	114	487
Example 41	116	473
Example 42	117	477
Example 43	123	450
Example 44	127	486
Example 45	129	472
Example 46	131	481
Example 47	133	483
Example 48	135	466
Example 49	139	476
Example 50	142	455
Example 51	144	469
Example 52	145	487
Example 53	146	466
Example 54	151	479
Example 55	156	455
Example 56	157	473
Example 57	160	484
Example 58	163	477
Example 59	165	463
Example 60	168	458
Example 61	171	472
Example 62	176	466
Example 63	177	450
Example 64	184	475
Example 65	188	449
Example 66	190	487
Example 67	195	455
Example 68	200	453
Example 69	210	467
Example 70	211	462
Example 71	213	473
Example 72	215	471
Example 1-1	C1	435
Example 2-1	D1	437
Example 3-1	E1	440
Example 4-1	F1	438
Example 5-1	G1	433
Example 6-1	H1	449

As can be seen from Table 6, it was confirmed that the Td value of the heterocyclic compound of Formula 1 according to the present application was about 40° C. higher than when the compounds of Comparative Examples 1-1 and 2-1 were included. . This is that the substituent of carbazoles substituted on one benzene ring of dibenzofuran is a hole transport character moiety, and N-Het substituted on the 1st position of the other benzene ring of dibenzofuran is an electron It is a substituent having transport characteristics (Electron transport character moiety), and in addition, the trisubstituted compound having a substituent of Ar at the 3-position has thermal stability than the compound in which the disubstituted (Comparative Example 1-1 and Comparative Example 2-1) compound is In particular, it shows that it is excellent.

_{In particular, in the case of Examples 1 to 72 of Table 6, the T d} (95%) value compared to the other cases (Examples 1-1 to 6-1) corresponding to Chemical Formulas 2 and 3 according to the present application. It tends to be higher by about 10 to 40 °C, and thus has a characteristic particularly good thermal stability. That is, in the case of Formulas 2 and 3, the carbazole-based substituent is substituted at the 3rd or 4th position, and as two substituents are formed at the 1st and 3rd positions of the opposite benzene ring, the molecular weight increases and the stability of the structure itself is improved. It was confirmed that there were increasing characteristics.

Claims (12)

1. A heterocyclic compound represented by the following formula (1):

   [Formula 1]

   

   In Formula 1,

   N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N,

   R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and -NRR' or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or to form an aromatic heterocyclic ring,

   L, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,

   Ar is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; or -SiRR'R";

   Wherein R, R' and R" are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 is a heteroaryl group of

   a, d and e are the same as or different from each other and are each an integer from 0 to 4,

   b is an integer from 0 to 3,

   c is an integer from 0 to 2,

   When a to e are 2 or more, the substituents in parentheses are the same as or different from each other.
2. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 2 to 5:

   [Formula 2]

   

   [Formula 3]

   

   [Formula 4]

   

   [Formula 5]

   

   In Formulas 2 to 5,

   Definitions of R1 to R10, N-Het, Ar, L, L1, L2, a, b, c, d, and e are the same as those in Formula 1 above.
3. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 6 or Chemical Formula 7:

   [Formula 6]

   

   [Formula 7]

   

   In Formulas 6 and 7,

   The definitions of R1 to R10, N-Het, L, L1, L2, a, b, c, d, and e are the same as the definitions in Formula 1 above,

   Ar1 is a substituted or unsubstituted C6 to C60 aryl group,

   X is O or S;

   R11 to R15 are the same as or different from each other and each independently represent hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and -NRR' or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or to form an aromatic heterocyclic ring,

   The definitions of R, R', and R" are the same as those in Formula 1 above,

   f is an integer of 0 to 3, and when f is 2 or more, the substituents in parentheses are the same as or different from each other.
4. The method according to claim 1, wherein N-Het of Formula 1 is a substituted or unsubstituted triazine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted 1,10-phenanthroline group; a substituted or unsubstituted 1,7-phenanthroline group; a substituted or unsubstituted quinazoline group; Or a substituted or unsubstituted benzimidazole group heterocyclic compound.
5. The heterocyclic compound of claim 1, wherein R9 and R10 are hydrogen.
6. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

   

   

   

   

   

   

   

   

   

   
7. a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises the heterocyclic compound according to any one of claims 1 to 6 Phosphorus organic light emitting device.
8. The organic light-emitting device of claim 7 , wherein the organic material layer includes an emission layer, and the emission layer includes the heterocyclic compound.
9. The organic light emitting device of claim 7 , wherein the organic material layer includes a light emitting layer, the light emitting layer includes a host material, and the host material includes the heterocyclic compound.
10. The organic light emitting device according to claim 7, wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound.
11. The organic light-emitting device of claim 7 , wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound.
12. The method according to claim 7, wherein the organic light emitting device is a light emitting layer, a hole injection layer, a hole transport layer. An organic light-emitting device further comprising one or more layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

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